Triethylamine → HCID 58247769, compound

HRID 714288Notes

Reaction equation

HRID 714288 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[CH2:13][CH2:14][N:15]=[C:16]=[O:17].C(N(CC)CC)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[O:17]=[C:16]1[NH:15][CH2:14][CH2:13][N:1]1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 160352-Chloroethyl isocyanateHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 58247769HCID 58247769, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-aminoisonicotinate (5.00 g, 32.9 mmol) and 2-chloroethyl isocyanate (4.51 g, 42.7 mmol) in anhydrous tetrahydrofuran (85 mL) was stirred at ambient temperature for 17 hours and refluxed for 3 hours, followed by the addition of triethylamine (10 mL) and potassium carbonate (9.60 g, 69.50 mmol). The reaction mixture was refluxed for 23 hours, cooled to ambient temperature and filtered. The solid residue was washed with water (2×20 mL hexanes (2×20 mL) and dried in vacuo to give methyl 2-(2-oxoimidazolidin-1-yl)isonicotinate as a colorless solid (4.22 g, 58%): 1H NMR (300 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.40 (d, J=5.1 Hz, 1H), 7.35-7.33 (m, 2H), 2.97 (t, J=7.5 Hz, 2H), 3.85 (s, 3H), 3.41-3.36 (m, 2H); MS (ES+) m/z 222.1.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureThe reaction mixture was refluxed for 23 hours
  3. filtrationfiltered
  4. washThe solid residue was washed with water (2×20 mL hexanes (2×20 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-437e218544364e9a816d45f98108a8d7
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

Loading…